U Up?
577 episodes - English - Latest episode: 2 days ago - ★★★★★ - 14K ratingsU Up? is the definitive modern dating podcast presented by Betches co-founder Jordana Abraham and comedian Jared Freid, where they discuss their take on the ebbs and flows of the crazy dating world we live in. From interpreting dating app interactions and weird sexual encounters, to defining the relationship and everything in between - they’re here to make sure you don’t die alone. For more fun dating commentary, polls, and bonus content, follow @u.up.podcast on Instagram. Become a friend (with benefits) of the podcast and subscribe to receive early release and ad-free versions of all our new episodes, plus bonus subscriber-only episodes. To sign up and become a friend (with benefits) today head to: subscribe.betches.com
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Episodes
Are Different Political Views A Deal Breaker?
September 19, 2021 04:00 - 35 minutesJared and Jordana are back with another Sunday Special, and this week’s episode is all about navigating political and cultural differences in dating. They start out with a conversation about how heightened political differences have manifested on dating apps. Then they answer an email from a listener about a guy she’s been seeing who has different opinions on heavy topics like guns. Do their differences mean they’re doomed? Plus they discuss how you should broach conversations about these top...
Can I Be Confident And Insecure At The Same Time? Ft. Violet Benson
September 15, 2021 04:00 - 1 hourOn this week’s episode, Jared and Jordana start out by recapping Jordana’s birthday celebration. An emailer writes in asking how to flirt IRL. How should she express interest outside of texting and social media? The Awkward Sexual Encounter involves a very hot car. Later, they answer an email from a listener asking how to be vulnerable with her partner about her insecurities. Finally, J&J are joined by Violet Benson, host of Too Tired To Be Crazy, to discuss her dating life and play a round o...
What Does A F*ckboy Get Out Of Being Friends?
September 12, 2021 04:00 - 34 minutesJared and Jordana are back with another F*ckboy or Nah? on this week’s Sunday Special. An emailer describes her situationship with a guy she met last October. At first he says he didn’t want a relationship and she was fine with that, but they continued to hang out and hook up. Eventually they have a DTR talk and he says he can see them dating in the future, but he needs to figure his own life out. Is he a f*ckboy for giving her hope for the future? Or should she have taken him at his original...
What To Do When You Let Your “Crazy” Show Too Soon Ft. Giannina Gibelli
September 08, 2021 04:00 - 1 hourOn this week’s episode, Jared and Jordana start out by answering an email from a listener who’s perfectly happy with her boyfriend except that she’s not physically attracted to him. Can attraction grow over time? Is it a deal breaker if it doesn’t? The Awkward Sexual Encounter is a bloody nightmare. Later, an emailer asks if she can recover from letting her “crazy” show too soon. Should she address it or just move on? Finally, J&J are joined by Love Is Blind star Giannina Gibelli to chat abou...
How Long Is Too Long To Wait For A Text Back?
September 05, 2021 04:00 - 30 minutesJared and Jordana are back with another Sunday Special. This week, an emailer writes in asking if long response times over text are always a bad sign. Do long messages make up for taking 48 hours to respond? Are these long waiting periods okay at any point in a relationship? Plus, they discuss what enthusiasm actually looks like over text. Learn more about your ad choices. Visit megaphone.fm/adchoices
Should I Accept A “Hangout” Date?
September 01, 2021 04:00 - 1 hourJared and Jordana start this week’s episode with a recap of Jordana’s trip to Greece, an update on Jared’s week of shows in Chicago, and Jordana’s feelings on the first Betches baby. A listener emails in asking if you can be too busy to date. Is it even worth it to schedule a date two weeks away? Or does she need to reprioritize? The awkward sex story involves a misplaced naked man. Later, an emailer asks how to go back to “real” dates after you’ve done a “hangout” date. Is there a more serio...
What You Should Ask Yourself Before You Break Up Ft. Logan Ury
August 29, 2021 04:00 - 48 minutesOn this week’s Sunday Special episode, Logan Ury, author of How To Not Die Alone and Director of Relationship Science at Hinge, is back to share more wisdom with Jared and Jordana. They start out with a discussion about post-pandemic dating from Logan’s research at Hinge and how it might be different from what “shot girl summer” predicted. Then, they discuss why we often look over the consistent, “nice” person and tips for going on dates the right way. Finally, they answer an email from a lis...
Lightning Round: Dating In The Age Of Social Media
August 25, 2021 04:00 - 1 hourJared and Jordana are back with your comprehensive guide to social media and dating. They answer 10 questions submitted by @uuppod Instagram followers and give real solutions to all of your social media issues, from how to craft the perfect DM to when to make your relationship Instagram official. Plus, they discuss which social media behavior should be a red flag. Learn more about your ad choices. Visit megaphone.fm/adchoices
Does Playing Games Ever Work?
August 22, 2021 04:00 - 24 minutesJared and Jordana are back with another Deal Reveal on this week’s Sunday Special episode. A listener shares screenshots of texts between her and a guy she had been dating for about 3 months. They met through mutual friends, but he was sketchy about her meeting his other friends. After an awkward situation where neither of them made the move to say hello in public, she decided to call it off. Did she overreact? Or did the situation prove that they’re looking for different things? Learn more a...
Why Would He Act Like My Boyfriend But Not Want To Date?
August 18, 2021 04:00 - 1 hourOn this week’s episode, Jared and Jordana start out with a chat about Jordana’s upcoming trip to Greece. Then, J&J answer an email from a listener for our newest segment, F*ckboy or Nah? Does honesty make someone exempt from f*ckboyhood? The Awkward Sexual Encounter is a mystery for Jared and Jordana to solve. Later, they answer an email about money etiquette when on vacation with your boyfriend’s family. Should you make an effort to pay for something or enjoy the hospitality? They finish the...
Can You Set Your Standard Too Low?
August 15, 2021 04:00 - 27 minutesJared and Jordana are back with another Deal Reveal on this week’s Sunday Special. The listener’s first date with a guy she met on a dating app went well, but the second date was rescheduled and the third was canceled. She sent a text setting her standard for following through on dates, and they ended up deciding to take things slow and keep it casual. Over a few weeks of being friends with benefits, his communication gets more and more inconsistent, and he ultimately tells her they can’t hoo...
How To Date Multiple People At Once
August 11, 2021 04:00 - 1 hourOn this week’s episode, Jared and Jordana start out with a discussion about the wedding industry and the fear of being judged. The first email asks how to juggle dating multiple people at once. When does she have to choose one guy to focus on? Does she need to tell them she’s dating around? The Awkward Sexual Encounter involves a dangerous food fetish. Later, J&J answer another email from a listener asking how she should bring up that she’s unsure about having kids. Finally, they play a round...
When Is It Time To Block Someone?
August 08, 2021 04:00 - 24 minutesJared and Jordana are back with another Sunday Special, and this week they’re talking about how to end it with a friend with benefits. A listener shares screenshots from her FWB who won’t take a hint that she’s no longer interested. Did she lead him on? How can she cut ties without feeling guilty? Plus they discuss the female version of a f*ckboy. Learn more about your ad choices. Visit megaphone.fm/adchoices
What Does Being A F*ckboy Actually Mean?
August 04, 2021 04:00 - 1 hourOn this week’s episode, Jared and Jordana discuss a DM Jared received asking whether or not a guy is a f*ckboy, which prompted the question: “What is a f*ckboy anyway?” J&J break down what actually makes someone a f*ckboy and where a lot of people get the definition wrong. The Awkward Sexual Encounter involves an infection in an unexpected area. Later, an emailer asks how to break off a relationship with her professor without getting anyone in trouble or impacting her grades. Finally, they pl...
Your Love Language Is Whatever You’re Getting The Least
August 01, 2021 04:00 - 26 minutesJared and Jordana are back with another Sunday Special all about love languages. Jared starts by explaining why he doesn’t like them, and then they answer an email from a listener who asks how to get more words of affirmation from her husband. Is it annoying for her to keep asking? Plus, Jordana shares a similar issue she had with her fiancé and how she dealt with it. Learn more about your ad choices. Visit megaphone.fm/adchoices
Is Cheating Always A Deal Breaker?
July 28, 2021 04:00 - 1 hourOn this week’s episode, Jared and Jordana start with a discussion about what makes a good first date. The first emailer asks if she should change one of her Hinge prompts. Will some guys always try to make it sexual or is her prompt putting out that vibe? A listener’s romantic vacation goes to sh*t in the Awkward Sexual Encounter. Later, they answer an email from a listener whose boyfriend of 10 years cheated on her. Can they still make it work? Finally, they play a round of Red Flag or Deal ...
How To Date In Your Twenties Ft. Dr. Meg Jay
July 25, 2021 04:00 - 50 minutesOn this week’s Sunday Special, Jared and Jordana are joined by Dr. Meg Jay, author of The Defining Decade. They start out with a discussion about how the phrase “30 is the new 20” has affected twenty-somethings’ mindsets and how gender stereotypes play into dating problems. Later, Dr. Jay explains how the “strength of weak ties” can help you meet your match. Finally, they answer an email from a listener who asks if it’s even worth it to date in your early twenties when so much of your future ...
Why Am I Offended If I Don't Even Like Him?
July 21, 2021 04:00 - 1 hourJared and Jordana start this week’s episode with a conversation about Jordana’s pre-wedding feelings and prep. The first email is from a listener whose ego is bruised after a guy she thought was really into her updated his dating app profile. They’re not exclusive, and she’s still using the apps, so why does it still feel personal? The Awkward Sexual Encounter involves an unfortunate butt dial. Later, an emailer asks how to set boundaries when her boyfriend lives with his parents. Should he b...
How To Know If The Timing Is Off Or If They're Just Not That Into You
July 18, 2021 04:00 - 27 minutesOn this week’s Sunday Special, Jared and Jordana break down the text messages between a listener and a guy she met through mutual friends at a wedding. After 3 dates, he sends her a text saying he’s not ready for a new relationship after his last ended, but that he’ll let her know when he’s ready to “pursue.” Is there still hope for something in the future? Or is he just letting her down easy? Learn more about your ad choices. Visit megaphone.fm/adchoices
Lightning Round: Your Summer Dating Questions Answered
July 14, 2021 04:00 - 1 hourOn this week’s episode, Jared and Jordana are back with another Lightning Round answering 10 questions submitted by our Instagram followers all about summer dating with topics ranging from group dates to vacation communication. Plus, they discuss how to meet people off the apps and whether or not serious relationships are possible during IRL Summer. Learn more about your ad choices. Visit megaphone.fm/adchoices
What To Do When You Catch Feelings And They Don’t
July 11, 2021 04:00 - 23 minutesJared and Jordana are back with another Deal Reveal on this week’s Sunday Special. A listener shared screenshots of her conversation with a guy she was seeing long-distance for about two months. It was supposed to be casual, but she caught feelings and his reaction was confusing. If he says he didn’t want to end things, why would he still be using Tinder? Can she still bring this up even if they haven’t put a label on it? Plus, they discuss what it actually means to use someone. Learn more ab...
Why Don’t My Friends Like The Guy I’m Seeing? Ft. Iliza Shlesinger & Margaret Cho
July 07, 2021 04:00 - 1 hourOn this week’s episode, J&J start out with a recap of Jordana’s bachelorette party. The first emailer asks how she should respond to her friends’ concerns about a guy she’s seeing. Why won’t they elaborate on their warnings? And should she give him a chance to explain himself? A listener’s fiancé confesses a dirty little secret during the Awkward Sexual Encounter. Then, a listener asks if you can get back together if the breakup was for mental health reasons. Should he reach out or let it go?...
Am I Settling Or Did I Just Find The Right Person Early? Ft. Lori Gottlieb
July 04, 2021 04:00 - 36 minutesOn this week’s Sunday Special, Jared and Jordana are joined by psychotherapist and author Lori Gottlieb. They start out with a discussion of what type of relationship issues Lori sees in therapy and how COVID has impacted them. Then they get into Lori’s book Marry Him and what you should actually look for in a long-term partner. Later, they answer an email from a listener who is anxious about planning a future with her boyfriend. Is it normal for her to feel she should date around more? How c...
How To Tell If A F*ckboy Has Actually Changed
June 30, 2021 04:00 - 1 hourOn this week’s episode, Jordana and Jared start out with a tale about Jordana’s phone and her plans for her bachelorette party. Then they answer an email from a listener asking if a f*ckboy can change his ways. Does him not wanting to hook up mean he’s more into her or less? The Awkward Sexual Encounter almost ended with penis surgery. Then (content warning) at around the 49 minute mark, a listener shares a story about being harassed by a stranger and asks how to turn down men when they hit o...
Am I Being Avoidant Or Do I Just Not Like Him?
June 27, 2021 04:00 - 27 minutesOn this week’s Sunday Special, Jared and Jordana are breaking down the texts between a listener and a guy she ended things with after six weeks because he never wanted to sleep over. Did she end it too soon? Or did she never really like him in the first place? Plus they discuss miscommunication when it comes to dating expectations. Learn more about your ad choices. Visit megaphone.fm/adchoices
How To Keep Your Summer Fling From Fizzling Ft. Jared’s College Ex, Ashley Bisman
June 23, 2021 04:00 - 1 hourOn this week’s episode, J&J start with an email from a listener asking how to keep the dating momentum going while you’re traveling. Should she try to keep in contact while she’s out of town? The Awkward Sexual Encounter is a dinner disaster. Later, a listener asks how to deal with being stereotyped by people she’s dating. Are stereotypes the real reason this guy doesn’t want to take her hiking? Finally, Jared and Jordana are joined by Jared’s college ex and author Ashley Bisman for a round o...
Should I Call Out A Breadcrumber?
June 20, 2021 04:00 - 22 minutesOn this week’s Sunday Special, J&J answer an email from a listener about how to deal with breadcrumbing. Should you call the breadcrumber out? Are you also a breadcrumber for continuing the conversation? Plus they discuss how to take control of your dating life. Learn more about your ad choices. Visit megaphone.fm/adchoices
Is It Weird To DM Someone If You Didn’t Match On The Apps?
June 16, 2021 04:00 - 1 hourOn this week’s episode, Jared and Jordana start out with a discussion about freezing your eggs and what it means for dating. Then they answer a listener's email about sliding into someone’s Twitter DMs. Can Twitter DMs be used for dating like Instagram? What should she say to make her move? An emailer finds a surprise in her sink during the Awkward Sexual Encounter. Later, a listener asks how to compromise on decor when moving in with your significant other. What can differences in decor styl...
Is Infidelity Inevitable? Ft. Dan Savage
June 13, 2021 04:00 - 55 minutesOn this week’s Sunday Special, Jared and Jordana are joined by relationship and sex columnist Dan Savage. They start out with a discussion of how Dan’s advice has evolved over the past 30 years and his thoughts on monogamy. Later, they answer an email from a listener whose ex-boyfriend left her for the same woman they had a threesome with. How should she approach threesomes in her current relationship? Plus, they discuss how to develop trust and boundaries in an open relationship. Learn more ...
Do I Have What It Takes To Have A Hot Girl Summer?
June 09, 2021 04:00 - 1 hourJared and Jordana start this week’s episode with a conversation about the world opening back up when you’re single versus when you’re in a relationship. Then they read a break up contract sent to a listener by her now ex-boyfriend. Can you take a long-term relationship back to a short-term relationship? How do finances play into a breakup? A listener learns about blue balls in the Awkward Sexual Encounter. Later, J&J answer an email asking exactly how to have a hot girl summer. Finally, Dylan...
Why Do Exes Come Back Pretending To Want Friendship
June 06, 2021 04:00 - 24 minutesJared and Jordana are back with another Deal Reveal on this week’s Sunday Special. This week’s emailer wants to know if her ex actually wants to be friends or if there’s another reason for him staying in touch. Is it ever a good idea to stay friends with an ex? J&J break down why he’s holding onto the friendship and what she should do about it. Learn more about your ad choices. Visit megaphone.fm/adchoices
Lightning Round: Dating App Pictures, Bad Kissers, And Emotionally Slutty Boyfriends
June 02, 2021 04:00 - 1 hourOn this week’s episode Jared and Jordana are back with another Lightning Round, answering 20 questions submitted by our Instagram followers with topics ranging from first date conversations to spicing up long-distance relationships. Plus, they discuss the best pictures to use on dating apps and how to correct someone’s kissing style. Learn more about your ad choices. Visit megaphone.fm/adchoices
Are Personality Types Relevant In Dating?
May 30, 2021 04:00 - 20 minutesJ&J are back with another Sunday Special all about personality types and how they factor into dating. They answer an email from a Type A listener with a Type B boyfriend who doesn’t know how to deal with their differences. Do these personality types actually determine compatibility? Do opposites attract or are their differences in cleanliness and punctuality a deal breaker? Plus, they discuss how to assess which qualities are most important to you in a partner. Learn more about your ad choice...
How To Hit On Someone Without Being Creepy Ft. Camille Kostek
May 26, 2021 04:00 - 1 hourOn this week’s episode, Jared and Jordana start out with a pep talk for going back out into the world. Then they answer an email from a listener who doesn’t know if she should ask someone out at their workplace. Is there an appropriate way to show someone you’re interested without making them uncomfortable? A listener gets an unpleasant surprise during the Awkward Sexual Encounter. Later, they weigh in on an email from a listener wondering what it means for her relationship that she actually ...
Is Alcohol F*cking Up My Dating Life?
May 23, 2021 04:00 - 31 minutesJordana and Jared are back with another Sunday Special, and this week they’re reading texts from a listener who thinks she might have ruined her chances with a dating app match by drunk texting him. The emailer describes her previous pattern of drinking too much and scaring guys off with her drunk texts, but she got it together during quarantine and finally feels ready to get back out there. That is until a night out with her coworkers. How should she address the drunk texts? And should she t...
Dealing With A Breakup
May 19, 2021 04:00 - 1 hourJ&J start the show with a conversation about Jared’s relationship status. The Awkward Sexual Encounter involves a 69 gone wrong. Later, they answer a listener email about a guy who wants to be in a one-sided open relationship. Is it a red flag that he wants her to sleep with other people? Jared and Jordana finish the episode with a round of Red Flag or Deal Breaker about vaping, voice messages, and airport hygiene. Learn more about your ad choices. Visit megaphone.fm/adchoices
How To Tell Your Best Friend You Have Feelings For Them Ft. Tinx
May 16, 2021 04:00 - 54 minutesOn this week’s Sunday Special, Jared and Jordana are joined by Tinx, and they start with a discussion about the differences between dating in NYC, LA, and San Francisco. Then they dive into Tinx’s dating life and her Box Theory about the right time to sleep with someone you’re dating. Later, they answer a listener’s email asking if she should tell her best friend she has feelings for him, and Tinx shares her personal experience of falling in love with her best guy friend. Learn more about you...
Will My Relationship Survive After The Pandemic?
May 12, 2021 04:00 - 1 hourJared and Jordana are back with another episode, and they start out with a discussion of the viral video of Ben Affleck shooting his shot with a woman who unmatched him on Raya. The first email asks how to deal with going back to the office when her boyfriend wants to continue their nomadic pandemic lifestyle. The Awkward Sexual Encounter involves three condoms and a dog. Later, J&J try to figure out why a guy bailed on a listener in the middle of their first date. They finish the episode wit...
A Matchmaker’s Guide To Finding Love Ft. Matchmaker Maria
May 09, 2021 04:00 - 57 minutesOn this week’s Sunday Special episode, Jared and Jordana are joined by Matchmaker Maria. They start out with a discussion about how Maria got into matchmaking and how she applied her matchmaking strategies to meeting her own husband. Maria breaks down how the matchmaking process works, the types of guys who hire matchmakers, and how men and women differ when it comes to matchmaking. Later, Maria explains when to have sex with someone new using her 12 date rule, and they answer an email asking...
Is Faking An Orgasm Anti-Feminist?
May 05, 2021 04:00 - 1 hourThis week, Jared and Jordana start out with a discussion about experimenting with your look. The first email asks about the etiquette of orgasms. Is it ever okay to fake it? The Awkward Sexual Encounter is almost too gross to believe. Later, an emailer asks J&J to sort out her boyfriend’s shady phone behavior. Is it always a bad sign if your S.O. doesn’t want to share their passcode? Finally, they finish the episode with a round of Red Flag or Deal Breaker that sparks a discussion about someo...
Not Everyone Who Doesn’t Want To Date You Is A F*ckboy
May 02, 2021 04:00 - 29 minutesJared and Jordana are back with another Sunday Special, and this week they’re breaking down texts from a “verbose fuckboy.” The listener received some very lengthy text messages from someone she was dating essentially saying, “it’s not you, it’s me.” Does his long explanation and apology mean he is being genuine? Or is he just like other guys who run at the first sign of a serious relationship? Plus, they discuss what actually makes someone a f*ckboy. Learn more about your ad choices. Visit m...
How To Have Casual Hookups Without Feeling Disrespected
April 28, 2021 04:00 - 1 hourOn this week’s episode, Jared and Jordana start out with a conversation about the energy in NYC and the post-pandemic dating scene. The first email asks how to have casual relationships without feeling disrespected. Are they always just about 2AM booty calls? The Awkward Sexual Encounter involves a bed wetter and an early morning streak across a college campus. Later, a listener writes in hypothesizing that you shouldn’t date someone who’s new to your city if you’re looking for a serious rela...
Is My Coworker Flirting Or Just Being Friendly?
April 25, 2021 04:00 - 37 minutesJared and Jordana are back with another Sunday Special, and this week they’re talking all about relationships with coworkers. An emailer writes in wanting to know if her work crush is flirting with her or just being friendly after their first Zoom meeting felt more like a first date and he offered to help her move. Should she make another move after her initial ask for drinks fell through? Plus, they share their general advice for navigating romantic relationships at work. Learn more about yo...
What You Should Know Before You Pay For Dating App Features
April 21, 2021 04:00 - 1 hourOn this week’s episode, Jared and Jordana start out with a conversation about the paid bonus features on dating apps and if using them makes you look desperate. Would you be turned off by someone sending you a Hinge rose? This week’s Awkward Sexual Encounter is surprisingly nutritious. Later, an emailer writes in asking how to find an “ass-smacking nice guy” after not feeling the sexual chemistry on first dates. Is there a middle ground between the guy who’s too shy to make a move and the guy...
Is He Bad At Planning Or Does He Just Not Care?
April 18, 2021 04:00 - 29 minutesJordana and Jared are back with another Sunday Special, and this week they’re dissecting texts between a listener and a guy who keeps rescheduling their dates. The emailer thinks the chemistry is there but worries he’s only looking to hook up. How many chances should you give someone to schedule a real date? Should she give him another chance if he reaches out again? Plus, they discuss how to know if a guy is taking you seriously. Learn more about your ad choices. Visit megaphone.fm/adchoices
Are You Setting Your Standards Or Avoiding Rejection?
April 14, 2021 04:00 - 1 hourOn this week’s episode, Jared and Jordana start out with a discussion about adult braces and sharing your space with a significant other during quarantine. An emailer sends in a screenshot of a dating app conversation where she sets her standards of looking for a relationship, but she isn’t sure if the response is sincere. At what point does the “what are you looking for?” conversation actually matter? During the Awkward Sexual Encounter, a listener gets nostalgic about a water bed mishap. La...
How To Spot a Lazy Dater Before You Get In Too Deep
April 11, 2021 04:00 - 27 minutesJordana and Jared are back with another Sunday Special, and this week they’re discussing when you can assume exclusivity with someone you’re seeing. A listener writes in after her DTR conversation with a long-distance romance did not go as she hoped. Was she reading the signs all wrong? Plus, they talk about the clues that someone is a lazy dater. Learn more about your ad choices. Visit megaphone.fm/adchoices
Lightning Round: Dating App Tips, F*ckboy Streaks, And Running Into Exes
April 07, 2021 04:00 - 1 hourOn this week’s episode, Jared and Jordana change things up with a lightning round of questions submitted by our Instagram followers. Instead of our usual email format, they answer 20 questions with topics ranging from how to get excited about using the dating apps, to running into exes, to how to get your S.O. to go to therapy. Plus, they give their best tips for moving in with your partner, making a dating app profile, and reaching out to a fling that ended because of the pandemic. Learn mor...
Why Do People Still Get Married?
April 04, 2021 04:00 - 31 minutesJared and Jordana are back with another Sunday Special, and this week they’re talking about a listener’s unpopular opinion on marriage. The emailer doesn’t think marriage is right for him, not because he’s afraid of commitment but because he doesn’t think it holds the same value in a modern relationship. Is it okay to date without having the end goal of marriage? How should you explain that to your S.O.? Plus, J&J talk about the benefits of marriage today. Learn more about your ad choices. Vi...
How Long Should It Take For Them To Say “I Love You”?
March 31, 2021 04:00 - 1 hourThis week, Jared and Jordana start out with a discussion about a survey sent to a listener by two of his dating app matches. Is this actually a good way to get to know someone? Next, a listener writes in for help after she told her boyfriend she loved him and he didn’t say it back. Can you ever come back from that conversation if it doesn't go well? Later, an awkward date takes the joke too far in an Awkward Sexual Encounter. Another emailer asks for advice on getting back together with an ex...